Acetic Acid → HCID 22643508, compound

HRID 2414909Notes

Reaction equation

HRID 2414909 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO.ClCCl>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:15][CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 660364-ChlorobenzylamineHCID 740491-Methyl-4-piperidoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 22643508HCID 22643508, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 6344DichloromethaneSolvent

Procedure

1-Methyl-4-piperidone (566 mg, 5.0 mmol) was dissolved in 10 ml methanol and placed in 100 ml flask. 4-Chlorobenzylamine (708 mg, 5.0 mmol) was added. Mixture was stirred and Acetic acid (˜0.75 ml) was added until pH˜5. NaCNBH3 (628 mg, 10 mmol) was slowly added. Gas evolution observed. After magnetic stirring for 16 hrs methanol was partly removed on Rotavapor (40° C.). Dichloromethane, 2M NaOH and water were added until pH˜10. Phases were separated and aq. phase was then re-extracted with dichloromethane. Combined organic phases were dried over MgSO4. Concentration on Rotavapor (40° C.) yielded 1.14 g crude 47AKU-27. TLC (10% methanol in dichloromethane): Rf=0.3. HPLC-MS (Method A): M+=239.1 (MS(%)=96).

Workup

  1. customplaced in 100 ml flask
  2. customwas partly removed on Rotavapor (40° C.)
  3. additionDichloromethane, 2M NaOH and water were added until pH˜10
  4. customPhases were separated
  5. extractionaq. phase was then re-extracted with dichloromethane
  6. dry with materialCombined organic phases were dried over MgSO4
  7. concentrationConcentration on Rotavapor (40° C.)
  8. customyielded 1.14 g crude 47AKU-27

Sources & evidence

ORD record
ord-7af5886ad3694464b96e880d16d9c805
Source dataset
uspto-grants-2004_11
Patent number
US06815458B2

Reaction notes

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